JP6663349B2 - ナノ/マイクロサイズ無機種床上でのポリアリールエーテルケトン樹脂の合成方法 - Google Patents
ナノ/マイクロサイズ無機種床上でのポリアリールエーテルケトン樹脂の合成方法 Download PDFInfo
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- JP6663349B2 JP6663349B2 JP2016535086A JP2016535086A JP6663349B2 JP 6663349 B2 JP6663349 B2 JP 6663349B2 JP 2016535086 A JP2016535086 A JP 2016535086A JP 2016535086 A JP2016535086 A JP 2016535086A JP 6663349 B2 JP6663349 B2 JP 6663349B2
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- 229920006260 polyaryletherketone Polymers 0.000 title claims description 45
- 239000011347 resin Substances 0.000 title claims description 23
- 229920005989 resin Polymers 0.000 title claims description 23
- 238000000034 method Methods 0.000 title claims description 16
- 230000002194 synthesizing effect Effects 0.000 title claims 7
- 238000006243 chemical reaction Methods 0.000 claims description 30
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 claims description 30
- 239000002245 particle Substances 0.000 claims description 21
- 229910010272 inorganic material Inorganic materials 0.000 claims description 20
- 239000011147 inorganic material Substances 0.000 claims description 20
- 239000002131 composite material Substances 0.000 claims description 16
- 238000001308 synthesis method Methods 0.000 claims description 16
- LXEJRKJRKIFVNY-UHFFFAOYSA-N terephthaloyl chloride Chemical compound ClC(=O)C1=CC=C(C(Cl)=O)C=C1 LXEJRKJRKIFVNY-UHFFFAOYSA-N 0.000 claims description 15
- 239000011575 calcium Substances 0.000 claims description 14
- 229920001652 poly(etherketoneketone) Polymers 0.000 claims description 11
- 229920000642 polymer Polymers 0.000 claims description 11
- 229910018072 Al 2 O 3 Inorganic materials 0.000 claims description 8
- 239000001506 calcium phosphate Substances 0.000 claims description 8
- 229910000389 calcium phosphate Inorganic materials 0.000 claims description 8
- 235000011010 calcium phosphates Nutrition 0.000 claims description 8
- 239000000919 ceramic Substances 0.000 claims description 8
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 claims description 8
- 239000004696 Poly ether ether ketone Substances 0.000 claims description 7
- 229920002530 polyetherether ketone Polymers 0.000 claims description 7
- 238000006116 polymerization reaction Methods 0.000 claims description 7
- 229910003471 inorganic composite material Inorganic materials 0.000 claims description 6
- 229920008285 Poly(ether ketone) PEK Polymers 0.000 claims description 2
- 229910010413 TiO 2 Inorganic materials 0.000 claims description 2
- 230000015572 biosynthetic process Effects 0.000 claims description 2
- 238000003786 synthesis reaction Methods 0.000 claims description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 42
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 28
- 239000007787 solid Substances 0.000 description 21
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 14
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 14
- 239000012153 distilled water Substances 0.000 description 14
- 229910052757 nitrogen Inorganic materials 0.000 description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
- 239000000203 mixture Substances 0.000 description 8
- 239000012467 final product Substances 0.000 description 7
- 238000002156 mixing Methods 0.000 description 7
- 239000011521 glass Substances 0.000 description 6
- 239000000463 material Substances 0.000 description 6
- 238000000635 electron micrograph Methods 0.000 description 4
- 238000012986 modification Methods 0.000 description 4
- 230000004048 modification Effects 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- 229910004298 SiO 2 Inorganic materials 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 239000011859 microparticle Substances 0.000 description 3
- 239000002105 nanoparticle Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- 229920000049 Carbon (fiber) Polymers 0.000 description 2
- 239000004917 carbon fiber Substances 0.000 description 2
- 230000006866 deterioration Effects 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- -1 ether ketone ketone Chemical class 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- 239000011368 organic material Substances 0.000 description 2
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 2
- 238000012856 packing Methods 0.000 description 2
- 229920001643 poly(ether ketone) Polymers 0.000 description 2
- 239000002861 polymer material Substances 0.000 description 2
- 238000012545 processing Methods 0.000 description 2
- HBMJWWWQQXIZIP-UHFFFAOYSA-N silicon carbide Chemical compound [Si+]#[C-] HBMJWWWQQXIZIP-UHFFFAOYSA-N 0.000 description 2
- 229910010271 silicon carbide Inorganic materials 0.000 description 2
- 229910052581 Si3N4 Inorganic materials 0.000 description 1
- 229910021536 Zeolite Inorganic materials 0.000 description 1
- 238000005299 abrasion Methods 0.000 description 1
- 230000003471 anti-radiation Effects 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 239000002041 carbon nanotube Substances 0.000 description 1
- 229910021393 carbon nanotube Inorganic materials 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 239000000805 composite resin Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 230000002079 cooperative effect Effects 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 description 1
- 238000007336 electrophilic substitution reaction Methods 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 239000003365 glass fiber Substances 0.000 description 1
- 230000009477 glass transition Effects 0.000 description 1
- 239000010439 graphite Substances 0.000 description 1
- 229910002804 graphite Inorganic materials 0.000 description 1
- 229910052588 hydroxylapatite Inorganic materials 0.000 description 1
- 125000000468 ketone group Chemical group 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 239000008204 material by function Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- XYJRXVWERLGGKC-UHFFFAOYSA-D pentacalcium;hydroxide;triphosphate Chemical compound [OH-].[Ca+2].[Ca+2].[Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O XYJRXVWERLGGKC-UHFFFAOYSA-D 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 125000000843 phenylene group Chemical class C1(=C(C=CC=C1)*)* 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 229920002959 polymer blend Polymers 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- HQVNEWCFYHHQES-UHFFFAOYSA-N silicon nitride Chemical compound N12[Si]34N5[Si]62N3[Si]51N64 HQVNEWCFYHHQES-UHFFFAOYSA-N 0.000 description 1
- 229910052814 silicon oxide Inorganic materials 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 229920001169 thermoplastic Polymers 0.000 description 1
- 239000004416 thermosoftening plastic Substances 0.000 description 1
- 239000010457 zeolite Substances 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/34—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from hydroxy compounds or their metallic derivatives
- C08G65/38—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from hydroxy compounds or their metallic derivatives derived from phenols
- C08G65/40—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from hydroxy compounds or their metallic derivatives derived from phenols from phenols (I) and other compounds (II), e.g. OH-Ar-OH + X-Ar-X, where X is halogen atom, i.e. leaving group
- C08G65/4093—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from hydroxy compounds or their metallic derivatives derived from phenols from phenols (I) and other compounds (II), e.g. OH-Ar-OH + X-Ar-X, where X is halogen atom, i.e. leaving group characterised by the process or apparatus used
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- C—CHEMISTRY; METALLURGY
- C01—INORGANIC CHEMISTRY
- C01B—NON-METALLIC ELEMENTS; COMPOUNDS THEREOF; METALLOIDS OR COMPOUNDS THEREOF NOT COVERED BY SUBCLASS C01C
- C01B33/00—Silicon; Compounds thereof
- C01B33/113—Silicon oxides; Hydrates thereof
- C01B33/12—Silica; Hydrates thereof, e.g. lepidoic silicic acid
-
- C—CHEMISTRY; METALLURGY
- C01—INORGANIC CHEMISTRY
- C01F—COMPOUNDS OF THE METALS BERYLLIUM, MAGNESIUM, ALUMINIUM, CALCIUM, STRONTIUM, BARIUM, RADIUM, THORIUM, OR OF THE RARE-EARTH METALS
- C01F7/00—Compounds of aluminium
- C01F7/02—Aluminium oxide; Aluminium hydroxide; Aluminates
- C01F7/021—After-treatment of oxides or hydroxides
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- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/34—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from hydroxy compounds or their metallic derivatives
- C08G65/38—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from hydroxy compounds or their metallic derivatives derived from phenols
- C08G65/40—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from hydroxy compounds or their metallic derivatives derived from phenols from phenols (I) and other compounds (II), e.g. OH-Ar-OH + X-Ar-X, where X is halogen atom, i.e. leaving group
- C08G65/4012—Other compound (II) containing a ketone group, e.g. X-Ar-C(=O)-Ar-X for polyetherketones
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
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- C08J5/00—Manufacture of articles or shaped materials containing macromolecular substances
- C08J5/005—Reinforced macromolecular compounds with nanosized materials, e.g. nanoparticles, nanofibres, nanotubes, nanowires, nanorods or nanolayered materials
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- C08K3/00—Use of inorganic substances as compounding ingredients
- C08K3/01—Use of inorganic substances as compounding ingredients characterized by their specific function
- C08K3/013—Fillers, pigments or reinforcing additives
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- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K3/00—Use of inorganic substances as compounding ingredients
- C08K3/18—Oxygen-containing compounds, e.g. metal carbonyls
- C08K3/20—Oxides; Hydroxides
- C08K3/22—Oxides; Hydroxides of metals
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- C08K3/30—Sulfur-, selenium- or tellurium-containing compounds
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- C08K3/36—Silica
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
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- C08L71/00—Compositions of polyethers obtained by reactions forming an ether link in the main chain; Compositions of derivatives of such polymers
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- C08G2650/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G2650/28—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule characterised by the polymer type
- C08G2650/38—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule characterised by the polymer type containing oxygen in addition to the ether group
- C08G2650/40—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule characterised by the polymer type containing oxygen in addition to the ether group containing ketone groups, e.g. polyarylethylketones, PEEK or PEK
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- C08J2371/00—Characterised by the use of polyethers obtained by reactions forming an ether link in the main chain; Derivatives of such polymers
- C08J2371/08—Polyethers derived from hydroxy compounds or from their metallic derivatives
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- C08K3/18—Oxygen-containing compounds, e.g. metal carbonyls
- C08K3/20—Oxides; Hydroxides
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- C08K3/32—Phosphorus-containing compounds
- C08K2003/321—Phosphates
- C08K2003/325—Calcium, strontium or barium phosphate
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- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Inorganic Chemistry (AREA)
- Nanotechnology (AREA)
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- Polyethers (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Description
機械ミキサー、温度計および窒素導管付きの500mL三角フラスコの中にナノ/マイクロサイズ無機材料粒子(セラミックス、ガラス、リン酸カルシウム)、AlCl3およびジクロロエタンをそれぞれ入れて、高純度窒素を1〜2時間通し、−5〜−20℃まで低温冷却された時点でミキサーを起動する。そして、この温度の下で反応装置中の固体が全部溶けるまで維持する。N-メチル-2-ピロリドンとジクロロエタンの混合液、ジフェニルエーテル及びテレフタル酸塩化物(及び/又は塩化テレフタロイル)など三種類の反応試料を三角フラスコに順次入れて、この温度(−5〜−15℃)の下で1〜2時間反応させた後、反応システムの温度を15〜26℃に上げて引き続き10〜15時間反応させる。続いて、再び三角フラスコにジフェニルエーテルを入れて1〜5時間(好ましくは3時間)反応させ、最後にメタノールを三角フラスコに入れて、白色の固体を析出させる。蒸留水、メタノール、蒸留水の順序で白色の固体を洗浄し、最終生成物を80〜120℃にて10〜20時間乾燥する。これにより、本発明のポリアリールエーテルケトン樹脂複合材料が得られ、その産出率は90%以上に達する。
Claims (7)
- ナノ/マイクロサイズ無機材料粒子を高分子重合反応が発生する種床として、当該ナノ/マイクロサイズ無機材料粒子のベース表面上で、ジフェニルエーテルとテレフタル酸塩化物を重合させてポリアリールエーテルケトン樹脂を得て、ポリアリールエーテルケトン無機複合材料を得るステップを含み、
前記ナノ/マイクロサイズ無機材料は、セラミックス又はリン酸カルシウムを含み、
前記リン酸カルシウムには、少なくとも以下の成分:Ca(H 2 PO 4 ) 2 、Ca 3 (PO 4 ) 2 、Ca 3 (PO 4 ) 2 、Ca 5 (PO 4 ) 3 (OH)、Ca 5 (PO 4 ) 3 (OH)、Ca 10 (PO 4 ) 6 (OH、F、Cl又はBr) 2 、Ca 8 H 2 (PO 4 ) 6 ・5H 2 Oのうちいずれか1つが含まれることを特徴とする、ナノ/マイクロサイズ無機種床上でのポリアリールエーテルケトン樹脂の合成方法。 - 前記ナノ/マイクロサイズ無機材料粒子の直径が50μm未満となることを特徴とする、請求項1に記載のナノ/マイクロサイズ無機種床上でのポリアリールエーテルケトン樹脂の合成方法。
- 前記ポリアリールエーテルケトン樹脂には、少なくともポリエーテルケトン(PEK)、ポリエーテルエーテルケトン(PEEK)、ポリエーテルエーテルケトンケトン(PEEKK)、ポリエーテルケトンケトン(PEKK)及びポリエーテルケトンエーテルケトンケトン(PEKEKK)のうちいずれか一種を含むことを特徴とする、請求項1又は2に記載のナノ/マイクロサイズ無機種床上でのポリアリールエーテルケトン樹脂の合成方法。
- 前記セラミックスには、少なくとも以下の主要成分:Al2O3、BeO、ZrO2、MgO、TiO2、BC、SiC及びWCのうちいずれか一種が含まれることを特徴とする、請求項1〜3のいずれか1項に記載のナノ/マイクロサイズ無機種床上でのポリアリールエーテルケトン樹脂の合成方法。
- 前記合成方法には、前記ナノ/マイクロサイズ無機材料粒子をポリアリールエーテルケトン類高分子重合体単体の反応システムの中に入れて、ワンステップ重合反応によってポリアリールエーテルケトン無機複合材料を得るステップを含むことを特徴とする、請求項1に記載のナノ/マイクロサイズ無機種床上でのポリアリールエーテルケトン樹脂の合成方法。
- 得られた複合材料中の無機材料含有量を0〜100%(wt)に調節することを特徴とする、請求項1に記載のナノ/マイクロサイズ無機種床上でのポリアリールエーテルケトン樹脂の合成方法。
- ポリアリールエーテルケトン樹脂の重合温度を15〜26℃にコントロールすることを特徴とする、請求項1又は5に記載のナノ/マイクロサイズ無機種床上でのポリアリールエーテルケトン樹脂の合成方法。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
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CN201310613616.1A CN103665368B (zh) | 2013-11-28 | 2013-11-28 | 一种在纳米/微米尺度无机种床上的聚芳醚酮树脂低温合成方法 |
CN201310613616.1 | 2013-11-28 | ||
PCT/CN2014/091791 WO2015078330A1 (zh) | 2013-11-28 | 2014-11-20 | 一种在纳米/微米尺度无机种床上的聚芳醚酮树脂低温合成方法 |
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CN103665368B (zh) * | 2013-11-28 | 2017-01-11 | 张家港祥成医用材料科技有限公司 | 一种在纳米/微米尺度无机种床上的聚芳醚酮树脂低温合成方法 |
FR3039157B1 (fr) | 2015-07-22 | 2019-06-28 | Arkema France | Composition a base de polyarylene-ether-cetone (paek) stable a l'etat fondu et procede de stabilisation d'une telle composition |
CN108659206A (zh) * | 2017-03-27 | 2018-10-16 | 张家港祥成医用材料科技有限公司 | 一种高钙磷无机材料含量的有机无机纳米仿生复合材料的制备方法 |
CN108690189A (zh) * | 2017-04-07 | 2018-10-23 | 中国科学院苏州纳米技术与纳米仿生研究所 | 聚醚酮酮/羟基磷灰石复合材料、其制备方法与应用 |
CN109364305B (zh) * | 2018-11-27 | 2021-05-04 | 中国科学院兰州化学物理研究所 | 一种纳米或微米陶瓷颗粒填充的聚醚醚酮基人工关节材料 |
JP6901530B2 (ja) * | 2019-08-07 | 2021-07-14 | 株式会社フジクラ | 光通信部品用樹脂組成物及びこれを用いた光通信部品 |
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US3956240A (en) * | 1973-07-12 | 1976-05-11 | Raychem Corporation | Novel polyketones |
US4361693A (en) * | 1981-07-08 | 1982-11-30 | Raychem Corporation | Preparation of poly(arylene ketones) using thio- and dithiocarbonic acid derivatives |
DE3416455A1 (de) * | 1984-05-04 | 1985-11-07 | Lorenz-Polygon-Ausbau Gmbh, 4600 Dortmund | Fuer aus stahlprofilen, insbesondere aus gi-profilen zusammengesetzte tuerstoecke des streckenausbaus im berg- und tunnelbau zur kraftschluessigen verbindung je eines kappenendes mit einem schraeggeneigten stempel vorgesehener sicherheitskappschuh |
CA1246297A (en) * | 1985-03-11 | 1988-12-06 | Robert A. Clendinning | Process for preparing poly(aryl ether ketones) |
JPH04202526A (ja) * | 1990-11-30 | 1992-07-23 | Toyobo Co Ltd | 芳香族ポリケトン類およびその製造方法 |
DE4420784A1 (de) * | 1994-06-15 | 1995-12-21 | Basf Ag | Verfahren zur Reinigung von Polyarylenetherketonen |
DE4424039A1 (de) * | 1994-07-11 | 1996-01-18 | Basf Ag | Amphotere Metalloxide als Cokatalysator bei der elektrophilen Synthese von Polyaryletherketonen |
CN101067021A (zh) * | 2006-09-19 | 2007-11-07 | 张驰 | 纳米氧化铝改性聚芳醚酮聚合物及其纳米瓷膜漆 |
TW200705740A (en) * | 2006-10-20 | 2007-02-01 | Univ Nat Central | Manufacture method of nano-composite-proton semipermeable membrane with adjustable pores |
GB0625484D0 (en) * | 2006-12-21 | 2007-01-31 | Victrex Mfg Ltd | Composite material |
CN101519399B (zh) * | 2009-03-27 | 2012-05-23 | 武汉工程大学 | 芳香环状聚醚酮齐聚物及其制备方法 |
DE102010038986A1 (de) | 2010-08-05 | 2012-02-09 | Endress + Hauser Gmbh + Co. Kg | Kompositwerkstoff, Formkörper, elektronisches Gerät mit Formkörper, und Verfahren zur Herstellung für einen Formkörper |
CN103278886B (zh) | 2013-05-30 | 2015-05-13 | 上海理工大学 | 太赫兹双波长环路耦合器 |
CN103665368B (zh) * | 2013-11-28 | 2017-01-11 | 张家港祥成医用材料科技有限公司 | 一种在纳米/微米尺度无机种床上的聚芳醚酮树脂低温合成方法 |
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WO2015078330A1 (zh) | 2015-06-04 |
US10106652B2 (en) | 2018-10-23 |
JP2016538399A (ja) | 2016-12-08 |
CN103665368A (zh) | 2014-03-26 |
EP3075756A1 (en) | 2016-10-05 |
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US20160297929A1 (en) | 2016-10-13 |
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